HJC0152   Click here for help

GtoPdb Ligand ID: 12140

Synonyms: compound 11 [PMID: 23459613] | compound 11 [WO2014113467A1] | HJC-0152 | HJC-1-52 [3]
Compound class: Synthetic organic
Comment: HJC0152 was originally identified as an orally bioavailable compound with anti-cancer properties [1], and weak anti-viral activity [2]. Its chemical structure is based upon that of the signal transducer and activator of transcription 3 (STAT3)-inhibiting compound niclosamide. STAT3 is an oncology drug target, since excessive activation of STAT3 occurs in cancers, and is a perdictor of poor prognosis. Blocking STAT3 signalling in many cancer cell types induces growth arrest and promotes apoptosis. To mour knowledge there is no quantitative data that supports the direct interaction of HJC0152 with STAT3.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 107.49
Molecular weight 369.03
XLogP 3.27
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NCCOc1ccc(cc1C(=O)Nc1ccc(cc1Cl)[N+](=O)[O-])Cl
Isomeric SMILES NCCOc1c(cc(Cl)cc1)C(=O)Nc1c(Cl)cc(cc1)[N+](=O)[O-]
InChI InChI=1S/C15H13Cl2N3O4/c16-9-1-4-14(24-6-5-18)11(7-9)15(21)19-13-3-2-10(20(22)23)8-12(13)17/h1-4,7-8H,5-6,18H2,(H,19,21)
InChI Key DIMJVBOEXNWPOG-UHFFFAOYSA-N
References
1. Chen H, Yang Z, Ding C, Chu L, Zhang Y, Terry K, Liu H, Shen Q, Zhou J. (2013)
Discovery of O-Alkylamino Tethered Niclosamide Derivatives as Potent and Orally Bioavailable Anticancer Agents.
ACS Med Chem Lett, 4 (2): 180-185. [PMID:23459613]
2. Shamim K, Xu M, Hu X, Lee EM, Lu X, Huang R, Shah P, Xu X, Chen CZ, Shen M et al.. (2021)
Application of niclosamide and analogs as small molecule inhibitors of Zika virus and SARS-CoV-2 infection.
Bioorg Med Chem Lett, 40: 127906. [PMID:33689873]
3. Zhou J, Chen H, Shen Q. (2014)
Stat3 inhibitor.
Patent number: WO2014113467A1. Assignee: Board Of Regents, The University Of Texas System. Priority date: 15/01/2013. Publication date: 27/04/2014.